CN102781888B - 高度z-选择性烯烃复分解 - Google Patents

高度z-选择性烯烃复分解 Download PDF

Info

Publication number
CN102781888B
CN102781888B CN201080054100.2A CN201080054100A CN102781888B CN 102781888 B CN102781888 B CN 102781888B CN 201080054100 A CN201080054100 A CN 201080054100A CN 102781888 B CN102781888 B CN 102781888B
Authority
CN
China
Prior art keywords
pyr
nar
chcme
reaction
cases
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201080054100.2A
Other languages
English (en)
Chinese (zh)
Other versions
CN102781888A (zh
Inventor
理查德·R·施罗克
安妮·J·金
赵宇
玛格丽特·M·弗卢克
阿米尔·H·霍维达
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boston College
Massachusetts Institute of Technology
Original Assignee
Boston College
Massachusetts Institute of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boston College, Massachusetts Institute of Technology filed Critical Boston College
Priority to CN201510514660.6A priority Critical patent/CN105152838A/zh
Publication of CN102781888A publication Critical patent/CN102781888A/zh
Application granted granted Critical
Publication of CN102781888B publication Critical patent/CN102781888B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/64—Preparation of compounds containing amino groups bound to a carbon skeleton by disproportionation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/083—Syntheses without formation of a Si-C bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0286—Complexes comprising ligands or other components characterized by their function
    • B01J2531/0288—Sterically demanding or shielding ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/64—Molybdenum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/66—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B01J2540/225—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate comprising perfluoroalkyl groups or moieties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/40—Non-coordinating groups comprising nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CN201080054100.2A 2009-09-30 2010-09-30 高度z-选择性烯烃复分解 Expired - Fee Related CN102781888B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510514660.6A CN105152838A (zh) 2009-09-30 2010-09-30 高度z-选择性烯烃复分解

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12/571,036 2009-09-30
US12/571,036 US8362311B2 (en) 2009-09-30 2009-09-30 Highly Z-selective olefins metathesis
PCT/US2010/002644 WO2011040963A1 (en) 2009-09-30 2010-09-30 Highly z-selective olefin metathesis

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CN201510514660.6A Division CN105152838A (zh) 2009-09-30 2010-09-30 高度z-选择性烯烃复分解

Publications (2)

Publication Number Publication Date
CN102781888A CN102781888A (zh) 2012-11-14
CN102781888B true CN102781888B (zh) 2015-09-23

Family

ID=43498607

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201080054100.2A Expired - Fee Related CN102781888B (zh) 2009-09-30 2010-09-30 高度z-选择性烯烃复分解
CN201510514660.6A Pending CN105152838A (zh) 2009-09-30 2010-09-30 高度z-选择性烯烃复分解

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN201510514660.6A Pending CN105152838A (zh) 2009-09-30 2010-09-30 高度z-选择性烯烃复分解

Country Status (6)

Country Link
US (4) US8362311B2 (https=)
EP (1) EP2483224A1 (https=)
JP (2) JP5788392B2 (https=)
CN (2) CN102781888B (https=)
CA (1) CA2776035A1 (https=)
WO (1) WO2011040963A1 (https=)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7932397B2 (en) 2006-11-22 2011-04-26 Massachusetts Institute Of Technology Olefin metathesis catalysts and related methods
US8222469B2 (en) * 2009-07-15 2012-07-17 Massachusetts Institute Of Technology Catalysts and processes for the formation of terminal olefins by ethenolysis
US8362311B2 (en) * 2009-09-30 2013-01-29 Massachusetts Institute Of Technology Highly Z-selective olefins metathesis
EP2556078B1 (de) 2010-04-03 2014-09-24 Studiengesellschaft Kohle MbH Katalysatoren für die alkinmetathese
GB2486631A (en) * 2010-12-01 2012-06-27 Univ Sheffield Phenol/quinone boronic acids/esters and method of preparation thereof
DE102011012629A1 (de) 2011-02-28 2012-08-30 Studiengesellschaft Kohle Mbh Metallkomplexe des Molybdäns und Wolframs und ihre Verwendung als Präkatalysatoren für die Olefinmetathese
US8546500B2 (en) 2011-05-27 2013-10-01 Massachusetts Institute Of Technology Complexes for use in metathesis reactions
CN103797009B (zh) 2011-06-03 2017-04-26 麻省理工学院 Z‑选择性闭环复分解反应
WO2012171652A1 (en) 2011-06-17 2012-12-20 Ximo Ag Synthesis of vitamin e
ES2736603T3 (es) 2011-11-07 2020-01-03 Massachusetts Inst Technology Complejos de wolframio oxo alquilideno para la metátesis de olefinas selectiva de Z
JP2015506335A (ja) * 2011-12-20 2015-03-02 ディーエスエム アイピー アセッツ ビー．ブイ． ９−オクタデセン二酸からのアゼライン酸の製造方法
EP2703081B1 (en) 2012-09-04 2019-08-07 XiMo AG Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
CN105555402B (zh) * 2013-03-14 2019-03-22 西莫有限公司 复分解催化剂及使用该催化剂的反应
WO2014169014A1 (en) 2013-04-09 2014-10-16 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
WO2014172534A1 (en) 2013-04-17 2014-10-23 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US9441059B2 (en) 2013-06-20 2016-09-13 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US10071950B2 (en) 2013-07-12 2018-09-11 Ximo Ag Use of immobilized molybdenum- and tungsten-containing catalysts in olefin cross metathesis
US10427146B2 (en) 2013-10-01 2019-10-01 Ximo Ag Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis
GB201404468D0 (en) * 2014-03-13 2014-04-30 Givaudan Sa Process
GB201406591D0 (en) * 2014-04-11 2014-05-28 Ximo Ag Compounds
WO2016014954A1 (en) * 2014-07-25 2016-01-28 California Institute Of Technology Tandem z-selective metathesis / dihydroxylation
FR3039546B1 (fr) * 2015-07-31 2017-08-11 Ifp Energies Now Procede de metathese des olefines utilisant un catalyseur contenant du silicium et du molybdene
DE102015215997A1 (de) * 2015-08-21 2017-02-23 Evonik Degussa Gmbh Phenol-Aren-Kupplungsprodukt
CN105111228A (zh) * 2015-08-28 2015-12-02 南京大学 具有5,5′-联四氢萘酮骨架的手性磷酸及其制备方法
WO2017087710A2 (en) * 2015-11-18 2017-05-26 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
EP3376859B1 (en) 2015-11-18 2021-01-06 Provivi, Inc. Microorganisms for the production of insect pheromones and related compounds
EP3394074B1 (en) 2015-12-23 2019-10-09 XiMo AG Immobilized metal alkylidene catalysts and use thereof in olefin metathesis
WO2017214133A2 (en) 2016-06-06 2017-12-14 Provivi, Inc. Semi-biosynthetic production of fatty alcohols and fatty aldehydes
US10183899B2 (en) 2016-11-10 2019-01-22 Chevron Phillips Chemical Company Lp Normal alpha olefin synthesis using metathesis and dehydroformylation
HUE073559T2 (hu) 2017-02-17 2026-01-28 Provivi Inc Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül
MX382401B (es) 2017-05-17 2025-03-13 Provivi Inc Microorganismos para la producción de feromonas de insectos y compuestos relacionados.
WO2018220088A1 (en) 2017-05-30 2018-12-06 Ximo Ag Methods of making olefinic e- and z-isomers
US11123723B2 (en) 2018-02-26 2021-09-21 The Regents Of The University Of California Oxidative dehydroxymethylation of alcohols to produce olefins
EP3759063A1 (en) 2018-02-26 2021-01-06 Bischof, Steven M. Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
EP3976565A1 (en) * 2019-05-27 2022-04-06 Verbio Vereinigte BioEnergie AG Tungsten imido alkylidene o-bitet and o-binol complexes and use thereof in olefin metathesis reactions
US10995049B2 (en) 2019-07-19 2021-05-04 California Institute Of Technology Total synthesis of prostaglandin J natural products and their intermediates
WO2021163533A1 (en) * 2020-02-14 2021-08-19 University Of Florida Research Foundation, Incorporated Cyclic polyacetylene and methods of preparing the same
US12151993B2 (en) 2021-09-10 2024-11-26 Chevron Phillips Chemical Company Lp Selective 1-hexene/1-octene production with 1-decene
WO2023217684A1 (en) 2022-05-10 2023-11-16 Signify Holding B.V. Regulation of fruit set in peppers by dynamically adapting the led lighting spectrum

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009094201A2 (en) * 2008-01-25 2009-07-30 Trustees Of Boston College Catalysts for metathesis reactons including enantioselective olefin metathesis, and related methods

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4727215A (en) * 1985-09-25 1988-02-23 Massachusetts Institute Of Technology Catalyst composition for effecting metathesis of olefins
US5055628A (en) 1990-09-11 1991-10-08 Ethyl Corporation Preparation of alpha-olefin by ethenolysis
JP3067031B2 (ja) * 1992-04-03 2000-07-17 カリフォルニア インスティチュート オブ テクノロジー オレフィンメタセシス重合方法
US5639900A (en) * 1993-12-29 1997-06-17 Metton America, Inc. Thermally activated olefin metathesis catalyst precursor
US5672802A (en) * 1996-03-19 1997-09-30 Shell Oil Company Process for the preparation of alpha olefins
US5889128A (en) 1997-04-11 1999-03-30 Massachusetts Institute Of Technology Living olefin polymerization processes
US6121473A (en) 1998-02-19 2000-09-19 Massachusetts Institute Of Technology Asymmetric ring-closing metathesis reactions
US6346652B1 (en) 1998-07-13 2002-02-12 Massachusetts Institute Of Technology Asymmetric ring-closing metathesis reactions involving achiral and meso substrates
US6215019B1 (en) * 1998-09-01 2001-04-10 Tilliechem, Inc. Synthesis of 5-decenyl acetate and other pheromone components
US6271325B1 (en) 1999-05-17 2001-08-07 Univation Technologies, Llc Method of polymerization
US6727396B2 (en) * 2001-01-25 2004-04-27 Abb Lummus Global, Inc. Process for the production of linear alpha olefins and ethylene
DE10206845A1 (de) * 2002-02-19 2003-08-28 Basf Ag Modifiziertes Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung
US6939982B2 (en) 2002-05-15 2005-09-06 The Trustees Of Boston College Recyclable chiral metathesis catalysts
US7220886B2 (en) 2004-10-27 2007-05-22 Catalytic Distillation Technologies Olefin metathesis
EP2094711B8 (de) * 2006-09-25 2018-03-28 Forschungsverbund Berlin e.V. Strukturmimetika prolinreicher peptide und ihre pharmazeutische verwendung
US7932397B2 (en) 2006-11-22 2011-04-26 Massachusetts Institute Of Technology Olefin metathesis catalysts and related methods
FR2917406B1 (fr) * 2007-06-13 2012-08-03 Arkema France Procede de synthese de diacides ou diesters a partir d'acides et/ou d'esters gras naturels
CN101205242A (zh) * 2007-09-30 2008-06-25 埃沃尼克德古萨有限责任公司 含有n-杂环卡宾配体的钌的亚烷基络合物及其在烯烃复分解反应中作为高活性高选择性催化剂的用途
DE102009027603A1 (de) 2009-07-10 2011-01-13 Robert Bosch Gmbh Verfahren zur Koordination von zumindest einem Antriebsaggregat
US8222469B2 (en) 2009-07-15 2012-07-17 Massachusetts Institute Of Technology Catalysts and processes for the formation of terminal olefins by ethenolysis
US8362311B2 (en) 2009-09-30 2013-01-29 Massachusetts Institute Of Technology Highly Z-selective olefins metathesis
EP2534140B1 (en) 2010-02-08 2018-04-11 Trustees of Boston College Efficient methods for z- or cis-selective cross-metathesis
US8546500B2 (en) 2011-05-27 2013-10-01 Massachusetts Institute Of Technology Complexes for use in metathesis reactions
CN103797009B (zh) 2011-06-03 2017-04-26 麻省理工学院 Z‑选择性闭环复分解反应
ES2736603T3 (es) 2011-11-07 2020-01-03 Massachusetts Inst Technology Complejos de wolframio oxo alquilideno para la metátesis de olefinas selectiva de Z
CN105555402B (zh) 2013-03-14 2019-03-22 西莫有限公司 复分解催化剂及使用该催化剂的反应
WO2014169014A1 (en) 2013-04-09 2014-10-16 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
WO2014172534A1 (en) 2013-04-17 2014-10-23 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US20140330018A1 (en) 2013-05-01 2014-11-06 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US9441059B2 (en) 2013-06-20 2016-09-13 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
EP3019511B1 (en) 2013-07-12 2019-01-02 XiMo AG Immobilized metathesis tungsten catalysts and use thereof in olefin metathesis
EP3107655B1 (en) 2014-02-21 2024-05-08 Massachusetts Institute of Technology Catalysts and methods for ring opening metathesis polymerization

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009094201A2 (en) * 2008-01-25 2009-07-30 Trustees Of Boston College Catalysts for metathesis reactons including enantioselective olefin metathesis, and related methods

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes;Ismail Ibrahem et al.,;《J. AM. CHEM. SOC.》;20090227;第131卷(第11期);第3844页 *

Also Published As

Publication number Publication date
JP2015214571A (ja) 2015-12-03
WO2011040963A1 (en) 2011-04-07
US9079173B2 (en) 2015-07-14
US8362311B2 (en) 2013-01-29
EP2483224A1 (en) 2012-08-08
US20110077421A1 (en) 2011-03-31
CN105152838A (zh) 2015-12-16
US9713808B2 (en) 2017-07-25
JP2013506663A (ja) 2013-02-28
CA2776035A1 (en) 2011-04-07
JP5788392B2 (ja) 2015-09-30
US20160008802A1 (en) 2016-01-14
CN102781888A (zh) 2012-11-14
US20130274482A1 (en) 2013-10-17
US10173208B2 (en) 2019-01-08
US20170113984A1 (en) 2017-04-27

Similar Documents

Publication Publication Date Title
CN102781888B (zh) 高度z-选择性烯烃复分解
Wu et al. Reactions of ruthenium carbenes of the type (PPh3) 2 (X) 2Ru: CH-CH: CPh2 (X= Cl and CF3COO) with strained acyclic olefins and functionalized olefins
CN104428306B (zh) 新的钌络合物、其在复分解反应中的应用以及用于进行复分解反应的方法
CN105555402B (zh) 复分解催化剂及使用该催化剂的反应
KR101835170B1 (ko) Z-선택적 올레핀 복분해 촉매 및 이들의 합성 절차
Tang et al. Nickel (II) complexes bearing phosphinooxazoline ligands: Synthesis, structures and their ethylene oligomerization behaviors
EP2454219A2 (en) Catalysts and processes for the formation of terminal olefins by ethenolysis
Jia et al. Synthesis and reactivity of ruthenium hydride complexes containing chelating triphosphines. 4. Reactions of ruthenium hydride complexes containing triphosphines with olefins
Jones et al. Synthesis, structural characterization, and regioselective reactivity with alkyl iodides of rhodium octaethylporphyrin indium octaethylporphyrin complex
Musso et al. Cationic molybdenum oxo alkylidenes stabilized by N-heterocyclic carbenes: from molecular systems to efficient supported metathesis catalysts
Gaderbauer et al. Synthesis and structural diversity of oligosilanylzinc compounds
EP3749674A1 (en) Molybdenum oxo alkylidene compounds, methods of making the same and use thereof in metathesis reactions
Trnka et al. Ruthenium alkylidene complexes coordinated with tricyclohexylphosphine and heterocyclic N-donor ligands
Franzke et al. Synthesis of new serine-based phosphinooxazoline ligands and iridium complexes for asymmetric hydrogenations
DeGroot et al. t-Butyl and trimethylsilyl substituents in nickel allyl complexes: similar but not the same
Bijpost et al. Reaction of ether and thioether functionalised 1-Alkenes with the cationic permethylzirconocene olefin polymerisation catalyst [(η5-C5Me5) 2ZrMe]+. Molecular structure of the insertion product [(η5-C5Me5) 2ZrCH2CH (Me) CH2OEt]+
Lorber et al. Isomerization of 2-methyl-3-butyn-2-ol into prenal: mechanistic observations on tricomponent catalyst systems of the type Ti (OR) 4–CuCl–R′ CO2H. Crystal structure of [CuCl (Me2C (OH) C CH)] 4
Tejeda Vanadium Alkylidene Complexes for Olefin Metathesis
CN114206889A (zh) Z选择性烯烃复分解催化剂的新合成
Hodík Homogeneous and heterogeneous titanium complexes and their use for selective ethylene trimerization to 1-hexene
Napier Developing Dimetal Paddlewheel Complexes for Catalytic Applications
Varjas Phosphinimide Complexes of Molybdenum: Synthesis, and Reactivity of Metal-Element Multiple Bonds
Raya Nickel and Cobalt-Catalyzed Hydrofunctionalization Reaction of Alkene
Alvarez I. Progress Toward the Development of an Alkyl Heck Reaction II. Preparation of an Unusual Palladacycle
He NHC-Ligated Transition Metal Catalyzed Functionalized Olefin Synthesis

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20150923

CF01 Termination of patent right due to non-payment of annual fee